m-Chloroperbenzoic acid → 8-(1-Oxidopyridin-4-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1809855Notes

Reaction equation

HRID 1809855 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([OH:17])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:26])C=1>C(Cl)Cl>[O-:26][N+:1]1[CH:2]=[CH:3][C:4]([C:7]2([OH:17])[CH2:8][CH2:9][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:15][CH2:16]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 137720538-(4-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 667869078-(1-Oxidopyridin-4-yl)-1,4-dioxaspiro[4.5]decan-8-olYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.35 g (10 mmol) of 8-pyridin-4-yl-1,4-dioxaspiro[4.5]decan-8-ol (prepared following the procedure described in Example 7) in 20 mL of methylene chloride was added 2.6 g (15 mmol) of mCPBA. The reaction mixture was stirred at room temperature for 1.5 h. Direct chromatography on silica gel afforded the title compound (2.45 g, 98%).

Sources & evidence

ORD record
ord-5c6c9cede4884ee6b5a70180d33ae59e
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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